Volvo Ocean Race - Dawn Riley transformed into a leader

When it comes to breaking barriers in big-boat sailing, few women can be compared to Dawn Riley. She was the first woman to manage an America’s Cup campaign, and the first American, male or female, to sail in three America’s Cups and two Whitbread Round-the-World races.

Today, she serves as executive director of Oakcliff Sailing Center in Oyster Bay (N.Y.), a unique school that grooms the next generation of world-class sailors. But the bedrock of her leadership skills were developed during a round-the-world race that took place 20 years ago, in a grueling contest that for Riley was not unlike getting an MBA during a game of survival.

This month, Riley is reissuing the story of that seminal race with her book Taking the Helm, written with co-author Cynthia Goss. Her adventure memoir tells the tale of skippering the 60-foot Heineken in the Whitbread Round-the-World Race. The next running of this race, now called the Volvo Ocean Race, begins in Spain in October 2014.

'I am amazed at how relevant the lessons of Heineken still are,' said Riley. 'That race taught me how to lead, how to trust my own decisions, and how to overcome challenges—many of which threatened our lives … I hope a new generation of readers will become armchair sailors with this book and, like me, experience a great adventure while getting a crash course in what it means to take a leadership role.'

Taking the Helm tells the story of Riley and her crew in the 1993-94 Whitbread Round-the-World Race. Riley was telephoned after the first leg of this ocean marathon, when the crew on the only all-female entry in the race was riven by dissent, financial problems and personal conflicts; only a new captain could save this team from mutiny and lead the women to a successful finish. Riley quickly packed up her life and flew to Uruguay. After four days of hasty boat preparation and group training, the women set sail from sunny Punta del Este, unprepared for the perils of the treacherous Southern Ocean.

The crew not only braved near-hurricane-force winds, numbing temperatures and jagged icebergs in the face of physical injury, dwindling supplies, equipment failure and overall exhaustion; they also faced bitter dissent amongst their crew. In the end, these women traveled much farther than the race’s 32,000 miles: with each leg and each new test, they learned to rally under their captain’s leadership. In recounting how she took responsibility for the lives of eleven other women, Riley tells an extraordinary story of self-discovery within the gripping context of the world’s most demanding sailboat race.

Riley wrote Taking the Helm during a landmark era in women’s sailing. After competing with Heineken in the Whitbread, she relocated to San Diego to sail with America3, the first all-women’s America’s Cup team. In the 2000 America’s Cup, she used her leadership skills to launch and become CEO of the co-ed Cup team America True, which for Riley was the next evolution for women in sailing: the team set out to do something unique by finding the best sailor for each job on board, whether male or female. Leading a team of talented sailors hungry to compete on the world stage who earned their spots by talent and not gender remains a highlight of her career. But as Riley surveys the state of women in sailing today, she sees some amazing achievements but also slow progress for truly integrating women into the sport.

'Women have done great things in sailing—and will continue to do great things,' says Riley. 'But as with any disadvantaged group, realizing they are disadvantaged is the first step, and then it’s like a jolt, a wake-up call, and you make huge progress and have some successes; but you can get complacent and assume, we are just going to keep moving forward. That does not always happen. It takes energy, and it takes young people who will put themselves out there and make a difference.'

At Oakcliff Sailing Center—located 30 miles from mid-town Manhattan in Oyster Bay, New York—Riley is busy grooming those sailors. Oakcliff is a high-level training center with a specialty of teaching 15- to 30-year-olds to become leaders in the sport (other adult programs are also available).

Riley is the mastermind of the Oakcliff program, and in 2009 was contacted by the Lawrence sailing family of Long Island, who had amassed a fleet of boats and shoreside facilities. They asked Riley to propose ways they could utilize those assets. One of her ideas was to create a top-level educational center that would train sailors not only on the water, but teach them the many skills needed to become a leader in the sport—such as an understanding of sponsorship and the business of racing, boat construction and technology, teamwork, and leadership and management skills. Riley’s education was more a trial by fire: with Oakcliff, America now has a center where students learn all the skills needed to take a leadership role in competitive sailing.

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